Explore Appalachian Trail: Connecticut: Best Day Hikes - view hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

This month marks the 80th anniversary of the #AppalachianTrail, which passes through 14 states from Maine to Georgia. . With so many access points along its approximate 2,190-mile route, this trail is not only an excellent option for thru-hikers and section-hikers, but also day-hikers and those looking to escape into nature for a few hours. . To honor the Appalachian Trail, we have compiled a list state by state of some of our favorite day hikes along the AT. Check out this list for Connecticut and help us celebrate the legacy and natural wonder of this trail!

Appalachian Trail: Connecticut: Best Day Hikes Map

One of my favorites in the area!

Great for trail running!

Easy hike with two pretty outlooks and a small waterfall. Nice day hike, definitely worth checking out.

Awesome trail. But beware, hard means hard! Not for the newbie. Hiked it when it was raining and definitely wouldn’t have wanted to be in that situation without climbing and scrambling skills. Can get very dangerous, very quick. Especially the back side of Bear Mt. And the ascent to Mt Everett is no joke! But what a great experience! Will be doing it again soon.

Great hike with a unique payoff at Rand's View. Was lucky to have the meadow all to myself, as I arrived early. Unfortunately it was a bit misty and foggy in the distance so the view was not all it might have been. Still super cool. I didn't hike as far as the AllTrails route indicates, but I did check out Giant's Thumb and went a little beyond that, until I saw the trail heading steeply downhill. Mount Prospect view is nice, though not spectacular. But it's a good place to rest for a while before chugging along to Rand's View. Lots of nice ups and downs on this trail, but nothing too taxing.

This section of the AT is difficult, that’s for sure. Sometimes the gradual climbs seem to go on forever. But once you reach the top(s) you’re rewarded with the most spectacular views. The northbound scramble down from Bear Mountain is also challenging. I’d definitely recommend hiking poles.

There are plenty of active water sources (at least in springtime) and the trails are nicely marked with ample signage. The campsites are nicely maintained, but prepare to share the shelters with other hikers. For me this proved to be an awesome opportunity to swap stories with experienced AT thru-hikers.

All-in-all a fantastically rewarding hike!

nice trail with waterfalls, not many decent views but when you do see one it's amazing. give yourself about 5rs time and bring snacks.

1 month ago

what a great hike. Just when you thought you reached the top and saw great views, you walk a few more minutes and boom, more gorgeous views overlooking the mountains. we started out going right on the trail, nice incline not to steep, nice little waterfalls along the way on the opposite side of the loop wow, what gorgeous falls. In a couple spots the water was cascading over the rocks to create an awesome view. It was like the best was saved for last. overall a great hike with a good amount of views and lots of nice waterfalls to see.

beautiful serene walk

Great views from the summit. The hike up is a bit strenuous, but the way down is through a beautiful pine forest with the trail paralleling a beautiful brook.

Such a beautiful hike! Can't wait to go back once the leaves are on the trees! Can get pretty steep at parts but not for too long and the view is totally worth it.

I'm planning a hike here this year. is there a place to park?

Hiked from Bull's Bridge to Amy's Lookout and back, so I didn't do the full loop. Really nice easy walk along the Housatonic with some areas where you can get photos of the rapids, then once you get to the Anderson Bridge, where the Ten Mile River empties into the Housatonic things start getting a bit more challenging - sustained climb from there up to the Herrick Trail, with lots of stone steps. The two overviews from the Herrick Trail are definitely worth it. Really nice hike. On the way back I took the Homestead Trail (marked with blue blazes) from the Anderson Bridge.

I very much Enjoyed this hike. Not very difficult...great for folks with not much experience hiking as well as families. Calebs Peak is a wonderful spot to stop and enjoy the view south through the Housatonic valley...pack a lunch!!

Moderate hike with good views of the Housatonic River Valley. It was overcast when we went, but not hazy, and when we reached the last overlook, there was a rainbow over the valley, which was a nice touch.

Great moderate hike..started from small parking lot off of route 341. Went up and over both St John's ledges and Calebs peak. Took about 4 hours with a stop for lunch on Calebs Peak...plenty of rocks to sit on and enjoy the view south of the Housatonic Valley

Hiking to Caleb peak was about a 1 mile rock scramble with nice views at the top. We continued on the AT just to get some distance in, although views weren’t as nice after the peak. A good day hike!


Beautiful hike. I went straight through to Cornwall Bridge. Easy climb up Caleb’s peak. The rock scramble coming down St. John’s ledges is tricky so be aware of that. Really beautiful right by the Housatonic River once you get down the ledges (and flat!). My hike totaled 11.4miles from 341 to Rt 4.

we hiked this trail often while living in CT Very pleasant, running water... just enough challenge for older hikers

A friend and I did this hike yesterday. It was a sunny day and there was a lot of snow still on the ground. The hike was lovely and definitely a workout going up and a little hairy going down. Best to hold onto some branches and trees or avoid slippery rock faces and take the deep snow way around. All in all a great 2 to 2 1/2 hour hike. if anyone happens to go on the trail and finds a gray hat with a pompon, please contact me st 203 592 8403. I believe I lost it on the trail and would love to get it back!

Nice winter hike! The trail can be a little muddy and slippery when snow covered. Beautiful waterfalls and some steep section and rewarded with amazing views.

Loved this hike!! Gorgeous winter morning trip. After going over Ten Mile Hill the trip along the Ten Mile and Housatonic Rivers is beautiful...not too grueling of a hike but enough to get your heart rate up.

Great winter hike - loop trail is strenuous enough for a work out and quick enough (90-120 min) to squeeze into a busy day. Nice views of the surrounding hills and a few streams and small waterfalls. Trail is well marked and dovetails with the AT for ~0.5 mile.

Magical especially after a snowfall...

It was amazing. I only walked about 2 miles in but I intend on going back next weekend for the whole round trip. I’m looking forward to this hike. It is flat or downhill in most places so far, so deeming it Easy was definitely appropriate. Looking forward to doing it this weekend!!!

Not exactly an easy trail, not exactly a moderate trail either. Lots to see

Tough trail in spots - especially the climb up Mt Everett from the south. Beautiful scenery that is always changing during the hike. Sages ravine was especially beautiful.

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